As much as you may want to leave your team to their own devices, there are instances when they need a helping hand, with teams using the likes of battle cards, one-pagers, and sales scripts.

With many companies using OKRs for their sales team to track progress, sales reps need to be equipped with the materials they need to do their job properly and also educate themselves about your product.

Kelly Esten, VP of Product and Partner Marketing at Toast, gave her insights on effective sales enablement tools, measuring the effectiveness of sales enablement, amongst other useful snippets of expertise.

We’re afraid you’ve missed the boat to submit your question for this AMA, however, we have plenty of great AMAs scheduled. Check out what’s coming up here.


Q: What type of sales assets work best for you? We already cover a lot of the basics (i.e. battle cards, comparison sheets, demos, etc.), are there any out of the box sales enablement tactics you've tried and had great success with?

A: We do a lot of the things you mentioned (battle cards, demo scripts, and video demos). Our sales team leverages a lot of our online content, so it can be used directly by prospects and by our own sales team - things like comparison pages, blog posts, content assets, product pages, etc.

Also, we create some sales playbooks, which have been well received, especially for major segments we target (types of restaurants, for example), or for major product launches. These playbooks have all of the resources related to that segment or product in one place including messaging, links to assets, objection handling, ways to source leads, and so on.

Finally, in a COVID world, we are putting more emphasis on sales decks since most of our meetings are remote. This is new for us since traditionally you wouldn't walk into a restaurant and give a formal PowerPoint conversation.


Q: How does sales enablement work at Toast? Do you have a dedicated sales enablement team? If so, how does that work for you, i.e. where do you and their lines begin and end?

A: We do - there is a dedicated sales enablement team within sales, in addition to a lot of enablement work that happens on my team.

The way we work together is sales enablement is responsible for standing up forums or ways to reach sales (weekly training, team meetings, QBRs, in-person training, etc.), and we plug into those forums with the product, competitive, market intel and messaging content. They give us feedback on the content in development to ensure it will resonate with sales, fits into our sales methodology, and makes sure it's interactive and engaging. They also go out and repeat and amplify our training in smaller group settings.

Finally, they are responsible for some types of training, like sales skills training, where we have input on those types of training (e.g. around objection handling or discovery). We'd be coming up with the answers to objections or the types of discovery questions, but they're developing it as a skill.


Q: How often does product marketing touch base with sales at your org? At the moment, we have regular check-ins in the run-up to a new release, but outside of that, we probably only touch base every 6-8 weeks or so. On the one hand, I don't want to put in meetings for the sake of meetings, but on the other, I feel like we could and should be doing more to keep in touch and maintain that communication flow.

A: Daily! We are in constant contact with sales, and there's a bunch of ways we do this and levels we engage at.

From a meeting perspective, we do weekly product training, attend sales leadership weekly calls and then run a more formal monthly win/loss call where we are sharing insights from our team on what we're seeing in the data and they're sharing back what they're hearing from their reps. We also (in normal times) get together in person once a quarter for QBRs which include business reviews and training.

I've also set a "quota" for our team to do a certain number of ride alongs per month with sales. This allows them to hear their messaging live, hear objections from customers and prospects, and walk a mile in the sales team's shoes. This is a big hit with our team and with sales.

Finally, I'm constantly asking for feedback from top-performing reps and sales leaders on everything we do. The Slack conversations with sales are hourly - answering questions, getting their input on work in progress, etc. Nothing goes out to sales without the input of several reps and managers to make sure it will work for our team.


Q: How do you go about measuring your sales enablement efforts? I see a lot of people look at sales asset usage and/or run surveys with their sales guys, but just wondering if you had any new or different way?

A: That’s a great, tough question. The gold standard for measuring sales enablement efforts is to tie it directly back to a sales metric, so we try to do this whenever possible (although it's not always clear causation, to be fair).

It could be moving the needle on a new product attach rate or leads generated for a new product immediately following training. It could be something like improvement in demo>quote conversion rate after doing demo training or new demo scripts/videos.

We measure competitive win rate religiously and in a lot of detail - so when we run competitive campaigns or promotions against certain competitors, we can usually see a movement in win rate vs that competitor after our push. My team is also incentivized on sales productivity and win rate, so we try to tie everything we can back to that where possible.

We don't currently have a measurement on our sales asset usage, but that's something I'd love to be able to do - particularly to tie it to winning opportunities rather than just downloads.

Finally, we do a lot of testing and certifying of our reps after training, so pass rates of reps tell us whether or not our training was effective.


Q: What are some software products you recommend for sales enablement? Anything that helps reps get ramped to quota faster?

A: For ramping reps, in particular, we use an LMS (learning management system) to put them through training and quizzes to make sure they are going through and understanding our content.

We also use a weekly quizzing tool that is competitive across the whole sales team so they can stay fresh on their knowledge. Other than that, we're pretty basic, leveraging Google sites and Google Drive, Slack, and email to make sure they have the latest.

We do have a ton of software that optimizes sales productivity and we find we get a great ROI on that, but sales enablement has mostly been done by people to date!


Q: How do you coordinate with your company's Product Manager who's in direct connection with both the customer service and R&D? In this case, how could a Product Marketing Manager could better collaborate with the PM or better define the work boundary between PM and PMM?

Also, how do you set expectations for the work to be carried out by PM vs PMM based on those boundaries?

A: Great questions on the PM/PMM connection and this could be a whole topic on its own! Our PMs are in direct contact with sales, customer success, and all of the customer-facing teams, in addition to us. They need to be so they're getting a feel for the feedback on their product and what the customer needs are that they're solving for, so we try not to get in the way.

We've established "core teams" that have a PM and a PMM as well as representatives from each department that touches a product (ops, product, CS, etc.) that work together throughout the product life cycle. We've tweaked these over time and they work differently (and frankly better) in some product areas than others. But the core responsibilities of each team are generally consistent, with lots of collaboration and communication.

When it comes to sales enablement, though, PMM is the gatekeeper to sales for rolling out new products, features, and training. We often bring our PM friends with us to help deliver training and get products launched, but ultimately we are the final decision maker and owner on what assets make sense, the messaging and positioning, and the training material.


Q: What processes/software do you use to share sales enablement for internal and partner use? Particularly a challenge when in a fast-moving environment where sales enablement may need to be updated frequently.

A: We are so behind on this! Our primary method is email.

We send out a weekly email to sales, partners, resellers, and customer success (that's 4 different emails) with the latest marketing material, themes to share, etc.

We also use Slack to communicate to sales and have dedicated channels for each major product line where we launch new assets and products, answer questions, and share ideas.

We have just stood up an internal google site where we are consolidating sales assets so that everything is in one place, which we hope will be a stopgap until we get a sales enablement software tool in place. We have been evaluating a handful of vendors for over a year, but for several, mostly internal reasons haven't implemented anything yet.


Q: How do you measure ROI, or in this case impact on sales pipeline, of sales enablement activities? What would be some tactics and best practices you’d recommend?

A: For webinars, we're using those post-training quizzes to understand whether a particular training was effective, and then we're using sales metrics to understand whether a set of tactics (tools, assets, and training combined) are moving the needle on a particular topic.

For broader training programs such as in-person workshops, a weekly training series, etc. we're looking at trends over time. We went through a big growth phase at Toast in our sales team over the past few years, and we were able to continuously improve sales productivity despite dropping tenure and adding lots of new reps. We took this, in addition to feedback from sales, as an indicator that generally our enablement was working.


Q: I’m keen to get the most from my partner enablement content. How do you repurpose content you've created for your largest partners to your mid-market partners?

Toast also has an awesome Resource Center. What are the most effective ways to drive traffic to these tools? How do you measure the success of the Resource Center as a whole as well as the effectiveness of the content? Anything other than downloads and views?

A: On the partner front, we create a lot of content that isn't partner-specific, or can be easily repurposed from partner to partner, by swapping a logo, for example.

A lot of what we do is enable our partners the same way we enable our sales team - with weekly updates on new assets, new product launches, promotions, etc. so they feel in the loop on what's happening at Toast. We only build custom stuff for a handful of big strategic partners, who get dedicated marketing support. This is all laid out in our tiered partner program, so it's clear from the start - a lot of our partners work with us because of our GTM muscle, so they get more GTM support as they grow with Toast.

Most assets in our Resource Center are created for a certain campaign or use case outside of the resource center first. So, their primary measurement is MELs (marketing engaged leads) generated by them. You'll notice most of the assets are gated. Once they're created, we aggregate them in the resource center as a secondary place to put them so that our customers and prospects can see them all in one place. A lot of restaurants know Toast because of our content program first, and then of course hopefully go on to become customers!


Q: How are you making sure your enablement content is leading to engagement? How are you thinking about ToastNow and TakeOut/Delivery in the context of engagement on behalf of your partners?

A: One of the metrics we look at a lot is the adoption of certain product lines by rep. We see a lot of variation among our team as far as who is leveraging certain add-ons, financing, partner products, etc. and so this is one way we focus our enablement and measure its success.

We might have reps that are good at selling a particular solution or partnership share ideas with those who haven't adopted it yet. For example, as a follow-up to introducing a new product.